Journal of the Chemical Society. Perkin transactions II p. 1785 - 1792 (1984)
Update date:2022-08-22
Topics:
Crampton, Michael R.
Routledge, Paul J.
Golding, Peter
Kinetic and equilibrium data are reported for the reactions of 2,2',4,4',6,6'-hexanitrostilbene (HNS) with four aliphatic amines in dimethyl sulphoxide, and are compared with those for related aromatic nitro-compounds.With each amine the most rapid reaction involves ?-adduct formation by attack at the 3(3')-positions.With the primary amines, n-butylamine and benzylamine, isomerisation to the thermodynamically more stable 1(1')-adducts occurs.However, with the secondary amines piperidine and pyrrolidine, attack at the 1(1')-positions is not observed, and this is attributed to their high steric requirements.It is shown that the formation of ?-adducts may involve rate-limiting proton transfer from zwitterionic intermediates to amine.A slow reaction is observed between HNS and each amine and is likely to involve amine attack at the olefinic bond.
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